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Merck
CN

1357056

USP

Leflunomide Related Compound B

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide

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About This Item

Empirical Formula (Hill Notation):
C12H9F3N2O2
CAS Number:
Molecular Weight:
270.21
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:
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InChI

1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-

SMILES string

O=C(/C(C#N)=C(O)/C)NC1=CC=C(C(F)(F)F)C=C1

InChI key

UTNUDOFZCWSZMS-YFHOEESVSA-N

grade

pharmaceutical primary standard

API family

leflunomide

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... DHODH(1723)

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General description

Leflunomide Related Compound B (2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide is a malononitrilamide which is a water soluble metabolite of Leflunomide. It is considered as a noncompetitive inhibitor of dihydro-orotate dehydrogensae. This metabolite has been reported to initially target activated lymphocytes.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

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Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable


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Li-Xia Xiong et al.
Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology, 25(1), 16-19 (2009-01-08)
To observe the inhibitory effects of tyrosine kinases inhibitor A77 1726 on collagen generation induced by IL-13 in fibroblasts. The inhibition rate of fibroblast proliferation with different concentration of A77 1726 was observed by MTT method. The fibroblasts were divided
Takeo Sato et al.
Rheumatology (Oxford, England), 48(10), 1265-1268 (2009-08-05)
To elucidate the factors associated with poor prognosis of LEF-induced lung injury in patients with RA. The background and clinical and laboratory features of LEF-induced lung injury were examined and compared between patients who died of and who recovered from
Yu-cong Yuan et al.
Zhonghua yi xue za zhi, 91(10), 703-706 (2011-05-24)
To explore the therapeutic effects of leflunomide metabolite A771726 on high glucose-induced podocyte injury and understand its mechanism. The conditionally immortal human glomerular podocytes were divided into normal glucose group (NG), high glucose group (HG), mannitol group (MA), high glucose
Paola Montagna et al.
Annals of the New York Academy of Sciences, 1193, 30-35 (2010-04-20)
Rheumatoid arthritis (RA) prevalence is greater in females than in males, supporting estrogens as modulators of immune response. Leflunomide (LEF) is employed in the RA treatment. We studied the combinatory effects of LEF active metabolite A77 1726 (LEF-M) and 17beta-estradiol
Eva Bernhoff et al.
Journal of virology, 84(4), 2150-2156 (2009-12-04)
The immunomodulatory drug leflunomide is frequently used for treating polyomavirus-associated nephropathy, yet its antiviral mechanism is unclear. We characterized the effects of the active leflunomide metabolite A771726 (LEF-A) on the polyomavirus BK (BKV) life cycle in human renal tubular epithelial

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